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Volumn 61, Issue 26, 1996, Pages 9084-9085

Conversion of hydroxy nitriles to lactones using Rhodococcus rhodochrous whole cells

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

EID: 0030446695     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9616623     Document Type: Article
Times cited : (35)

References (37)
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    • 0001755803 scopus 로고
    • Wiley: New York
    • For representative examples see: (a) Prout, F. S.; Hartman, R. J.; Huang, E. P.-Y.; Korpics, C. J.; Tichelaar, G. R. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 93. (b) Allen, C. F. H.; Johnson, H. B. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 804. (c) McGuire, M. A.; Sorenson, E.; Owings, F. W.; Resnick, T. M.; Fox, M.; Baine, N. H. J. Org. Chem. 1994, 59, 6683.
    • (1963) Organic Syntheses , vol.4 COLLECT , pp. 93
    • Prout, F.S.1    Hartman, R.J.2    Huang, E.P.-Y.3    Korpics, C.J.4    Tichelaar, G.R.5
  • 11
    • 0007384072 scopus 로고
    • Wiley: New York
    • For representative examples see: (a) Prout, F. S.; Hartman, R. J.; Huang, E. P.-Y.; Korpics, C. J.; Tichelaar, G. R. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 93. (b) Allen, C. F. H.; Johnson, H. B. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 804. (c) McGuire, M. A.; Sorenson, E.; Owings, F. W.; Resnick, T. M.; Fox, M.; Baine, N. H. J. Org. Chem. 1994, 59, 6683.
    • (1963) Organic Syntheses , vol.4 COLLECT , pp. 804
    • Allen, C.F.H.1    Johnson, H.B.2
  • 12
    • 0028046117 scopus 로고
    • For representative examples see: (a) Prout, F. S.; Hartman, R. J.; Huang, E. P.-Y.; Korpics, C. J.; Tichelaar, G. R. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 93. (b) Allen, C. F. H.; Johnson, H. B. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 804. (c) McGuire, M. A.; Sorenson, E.; Owings, F. W.; Resnick, T. M.; Fox, M.; Baine, N. H. J. Org. Chem. 1994, 59, 6683.
    • (1994) J. Org. Chem. , vol.59 , pp. 6683
    • McGuire, M.A.1    Sorenson, E.2    Owings, F.W.3    Resnick, T.M.4    Fox, M.5    Baine, N.H.6
  • 13
    • 0025913667 scopus 로고
    • For representative examples of this transformation, see: (a) Gopalan, A.; Lucero, R.; Jacobs, H.; Berryman, K. Synth. Commun. 1991, 21, 1321. (b) Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc., Perkin Trans. 1 1979, 26.
    • (1991) Synth. Commun. , vol.21 , pp. 1321
    • Gopalan, A.1    Lucero, R.2    Jacobs, H.3    Berryman, K.4
  • 14
    • 0002633617 scopus 로고
    • For representative examples of this transformation, see: (a) Gopalan, A.; Lucero, R.; Jacobs, H.; Berryman, K. Synth. Commun. 1991, 21, 1321. (b) Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc., Perkin Trans. 1 1979, 26.
    • (1979) J. Chem. Soc., Perkin Trans. 1 , pp. 26
    • Matsuda, I.1    Murata, S.2    Ishii, Y.3
  • 15
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    • references cited therein
    • Sugai, T.; Katoh, O.; Ohta, H. Tetrahedron 1995, 51, 11987 and references cited therein.
    • (1995) Tetrahedron , vol.51 , pp. 11987
    • Sugai, T.1    Katoh, O.2    Ohta, H.3
  • 22
    • 12644301779 scopus 로고    scopus 로고
    • note
    • Purchased from Institute for Fermentation, Osaka (IFO), 17-85 Juso-honmachi 2-chome, Yodogawa-ku, Osaka 532, Japan.
  • 24
    • 12644300203 scopus 로고    scopus 로고
    • note
    • 4 reduction of commercially available 5-oxohexanenitrile.
  • 26
    • 12644265954 scopus 로고    scopus 로고
    • note
    • See Supporting Information for typical experimental procedure.
  • 32
    • 12644281394 scopus 로고    scopus 로고
    • note
    • As a control, substrate 1a was placed in the pH 6 buffer at 30 °C for 18 h. No 2a was detected by TLC or GC, and 1a was recovered quantitatively.
  • 33
    • 0001592575 scopus 로고
    • 1H NMR spectrum of 4-hydroxyhexanamide (3), which was prepared by partial chemical hydrolysis of 1a using the method of Rao: Rao, C. G. Synth. Commun. 1982, 12, 177.
    • (1982) Synth. Commun. , vol.12 , pp. 177
    • Rao, C.G.1
  • 34
    • 12644270769 scopus 로고    scopus 로고
    • note
    • Various microorganisms including Rhodococcus sp. have been shown to possess hydratase/amidase activity, nitrilase activity, or both (see refs 5-8). Although we cannot rule out the two-step hydratase/amidase mechanism, we have chosen to present our results within the context of a nitrilase mechanism.
  • 35
    • 12644298285 scopus 로고    scopus 로고
    • note
    • -1) in the IR and a very polar spot by TLC that dissappeared upon treatment with acid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.